Issue 11, 1992

Kinetics and mechanism of the condensation reaction of symmetrical and unsymmetrical 1,3-diketones with cyanoacetamide in the synthesis of 4,6-disubstituted-3-cyano-2-pyridones

Abstract

The rate constants for the condensation reaction of cyanoacetamide with pentane-2,4-dione, 5-methylhexane-2,4-dione and 5,5-dimethylhexane-2,4-dione catalysed by piperidine were determined under a variety of experimental conditions. A UV spectrophotometric method for rate measurements was developed and the structures of the products were elucidated by means of a spectroscopic study. On the basis of the obtained rate constants, activation parameters and the evidence on the structure of synthesized unsymmetrical 4,6-disubstituted-3-cyano-2-pyridones a possible reaction scheme was suggested. It was thus possible to explain the selectivity of the reaction and the position of substituents in the pyridones obtained.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1992, 1965-1970

Kinetics and mechanism of the condensation reaction of symmetrical and unsymmetrical 1,3-diketones with cyanoacetamide in the synthesis of 4,6-disubstituted-3-cyano-2-pyridones

M. Mišić-Vuković and M. Radojković-Veličković, J. Chem. Soc., Perkin Trans. 2, 1992, 1965 DOI: 10.1039/P29920001965

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